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Depends how you define "real money" but I have made over $10,000 some months with advertisers running paid ads on Emailaddresses.com. Less now since it's the quiet summer months, and I have fallen back on affiliate programs quite a bit...

Yes it is very possible to make a living on the web. Last month my main site made $3200 from ads and affiliate programs.

The problem is you will have to work hard and shell out money at first.

The thing you need is content. The old phrase "Build It And They Will Come" does not work on the internet. The new phrase should be "Build Something Unique That People Want And Then Work Your But Off To Promote It And They Will Come
"

I have to agree with ya there matt- it's definitely an important point- make a niche, give advertisers something unique- a unique audience, and they will most likely be interested in buying ads on your site.